Total synthesis of (+)-fumiquinazoline G and (+)-dehydrofumiquinazoline G

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 483-484

  He, Feng ^a   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003153862     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6137     Document Type: Article

References (23)

1. (a) Takahashi, C.; Matsushita, T.; Doi, M.; Minoura, K.; Shingu, T.; Kumeda, Y.; Numata, A. J. Chem. Soc., Perkin Trans. 1 1995, 2345-2353.
2. (b) Numata, A.; Takahashi, C.; Matsushita, T.; Miyamoto, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Inoue, M.; Ohishi, H.; Shingu, T. Tetrahedron Lett. 1992, 33, 1621-1624.
3. Wong, S. M.; Musza, L. L.; Kydd, G. C.; Kulling, R.; Gillum, A. M.; Cooper, R. J. Antibiot. 1993, 46, 545-553.
4. Barrow, C. J.; Sun, H. H. J. Nat. Prod 1994, 57, 471-476.
5. Büchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084-5086.
6. Ohnuma, T.; Kimura, Y.; Ban, Y. Tetrahedron Lett. 1981, 22, 4969-4972.
7. (a) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709-3710.
8. (b) Nakagawa, M.; Ito, M.; Hasegawa, Y.; Akashi, S.; Hino, T. Tetrahedron Lett. 1984, 25, 3865-3868.
9. (c) Nakagawa, M.; Sodeoka, M.; Yamaguchi, K.; Hino, T. Chem. Pharm. Bull. 1984, 32, 1373-1384.
10. Bock, M. G.; DiPardo, R. M.; Pitzenberger, S. M.; Homnick C. F.; Springer, J. P.; Freidinger, R. M. J. Org. Chem. 1987, 52, 1644-1646.
11. Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143-11144.
12. See reference 6b and reference 6 therein.
13. Takeuchi, H.; Hagiwara, S.; Eguchi, S. Tetrahedron 1989, 45, 6375-6386.
14. Use of D-tryptophan will lead to natural (-)-fumiquinazoline G.
15. Maryanoff, B. E.; McComsey, D. F.; Nortey, S. O. J. Org. Chem. 1981, 46, 355-360.
16. Ottenheijm, H. C. J.; Tijhuis, M. W. Organic Syntheses, Coll. Vol. VII, Freeman, J. P., Ed.; Wiley: New York, 1990, pp 467-469.
17. (a) Ottenheijm, H. C. J.; Plate, R.; Noordik, J. H.; Herscheid, J. D. M. J. Org. Chem. 1982, 47, 2147-2154.
18. (b) Plate, R.; Nivard, R. J. F.; Ottenheijm, H. C. J. J. Chem. Soc., Perkin Trans. 1 1987, 2473-2480.
19. (c) Plate, R.; Akkerman, M. A. J.; Ottenheijm, H. C. J.; Smits, J. M. M. J. Chem. Soc., Perkin Trans. 1 1987, 2481-2490.
20. Ardakani, M. A.; Smalley, R. K.; Smith, R. H. J. Chem. Soc., Perkin Trans. 1 1983, 2501-2506.
21. Yamaura, M.; Suzuki, T.; Hashimoto, H.; Yoshimura, J.; Okamoto, T.; Shin, C.-g. Bull. Chem. Soc. Jpn. 1985, 58, 1413-1420.
22. Epimerization at the CHMe center occurred during hydrolysis of the trifluoroacetamide with aqueous base.
23. Neklyudov, A. D.; Shchukina, L. A.; Suvorov, N. N. J. Gen. Chem. USSR 1967, 37, 747-750.